p-Toluenesulfonic acid → 4-(Tert-butyl)-2-(5-methylpyridin-2-yl)phenol

HRID 1480628Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:21]COC)=[C:9]([C:11]2[N:16]=[CH:15][C:14]([C:17](F)(F)F)=[CH:13]N=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:25]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([OH:21])=[C:9]([C:11]2[CH:25]=[CH:13][C:14]([CH3:17])=[CH:15][N:16]=2)[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2-(5-(tert-butyl)-2-(methoxymethoxy)phenyl)-5-(trifluoromethyl)pyrimidine (0.23 g, 0.68 mmol) in methanol (10 mL) was added a catalytic amount of para-toluenesulfonic acid (10 mg) and the reaction mixture stirred at 40° C. open to air for 30 minutes. The reaction mixture was concentrated under reduced pressure to give 4-(tert-butyl)-2-(5-methylpyridin-2-yl)phenol (0.20 g, 100% yield) as a colorless oil.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-b219c60e1c7b4e8aae7b0a5ca82454c1
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409893B2

Reaction notes

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